Colin Plamondon

I’m an automated pessimist.
  

Most of humanity sucks at estimating- I usually do pretty damn well. I know my multiple.

Most people are always off by a multiple.  2x, 3x- each person has their own personal margin of wrongness, and boy, is it consistent.

What I’ve found in financial projections, product plans, growth numbers, and thinking up new ventures is that I’m a 2x person. I’m incredibly accurate as soon as I halve my internal estimate. 

Two $100/day new products? Divide by two, two $50/day new products! Update should take two weeks? It’ll take four! Revenue should X by Y? 

Double it!

Entrepreneurs are always optimistic- that’s how you get a product from idea to protype to release and, eventually, success. However, that optimism also makes for shit planning processes. 

Take your optimism, find your multiple, and process your optimism into accuracy.

Lots of startupy folks talk about ‘Minimum Viable Products’, helpfully capitalized and abbreviated to ‘MVP’. This confuses sports people. 

Whatever. 

The idea is that your first version should be the REALLY first version. Anything that isn’t crucial to your core concept should be jettisoned into Version Infinity.

What I’ve noticed, though, is that it’s easy to talk a good game about MVPs, but incredibly difficult to followthrough.

If you have a good idea, though, you have enormous margin to play around with. In fact, that’s how I would define a great idea. A great idea is something so awesome, you can’t screw it up. 

We’ve never released a first version of Free Books with font resizing or night mode. The first version on iPad didn’t even have search. Why? We already had collections! 

Free Books = the easiest way to discover, download, and read books on the planet. Everything else? Screw it! That’s what updates are for.

With Browser+ we set out to build a full-screen browser that doesn’t suck. All our competitors take desktop browsers, throw em on a multitouch screen, and call it a day. Lazy, boring, and slow. We decided to focus on building a great fullscreen browsing experience. 

Toolbar is hidden on the side of the screen- swipe from the side to pull it out! Want Most Visited and Visual History? Just pull the toolbar farther. Where’s the address bar? Swipe from the bottom! It’s just you and the internet- no interruptions. See a link you want to read? Long hold it, and it’ll come up in an Overlay. Read it, close it, you’re right back where you were, no loading, no refreshing. 

That clarity of purpose let us jettison basic features like tabs and even bookmarking. The very first version of Internet Explorer had that! Yup. It’s a great feature. But it’s also not integral to making a great full-screen browsing experience. That’s why it’s going in our first update! Just not in the first version.

By making the decision to cut things as basic as search in a book app and bookmarking in a browser, we prove our ideas. If it’s really a great idea, people will put up with a lot- and let you know what sucks! With that feedback you can prioritize. We thought people would want tabs more than bookmarking. Turns out, by a margin of 400 emails, the answer is a resounding ‘bookmarking first!’. 

That saves us time, that saves us energy, and it lets us start generating revenue while working on implementing bookmarking first.

Bottom line- Minimum Viable Products are supposed to suck. If you can’t identify a key way in which your first release blows, you haven’t cut enough. Cut more. Cut deep. Cut until you’re embarrassed. If 40% of people don’t hate your product in the first version, you launched too late. 

If 100% of people hate your product in the first version now you know the problem- your idea sucks!

I'm still figuring out this whole travel thing.

Before, when I travelled, there were few barriers. Few commitments, few things to ground me in a single place.

Now? Spreadsong has turned into a real company. Hundreds of thousands of users, millions of installs, serious income. Our team has weekly calls. We have new products in development. I also have an apartment in Boston, with an office in Cambridge.

But above all is ambition. Just how much more we can do. New products, new experiences to build, new mountains to climb. As I write this I'm flying off to Medellin, Colombia. It's very different than when I headed to Koh Tao two years ago. I'm in First Class and have a whisky in hand, for one. It's also a three week trip- NYE in Medellin, work from from Bogota. It's not wanderlusting anymore- that isn't practical. It's more a reset. Take a few weeks working from a new country, meet tons of new friends, have insane experiences never to be digitally spoken of, and get some perspective.

Whenever I have a trip somewhere, long or short, some wicked new idea springs from it. Last time, when in hiked the Inca Trail, it was a complete reimagining of our strategy over the next six months. This time? Could just be a bad hangover. But more likely is a dot connection. Doing new things lends the raw material of creation- experience. Experiences connect in weird ass ways. Random comment by a person on a train, the design of a building you've never seen, an idea that bursts into being after an epic night out.

Flying still kicks ass. Is it the same as before starting a business? Hell no. But that's not a negative hell no- it's a different hell no. It's a time limited hell no. It's a better appointed hell no, to be sure. But largely, it's one hell of an experience packed hell no. 

Sent from my iPad

I was fortunate enough to have been recently featured in a really great article for  CNN.com, entitled 'Summer Chasers'. It turned out fantastically, and is actually a really cool read. Not because I'm in it, but, you know, it's actually a cool read. Check it out!

Prioritization? Eh. A lot of company blogs yap on about the 'startup life' or some nonsense.

It's more a matter of resource allocation. 

So many hours, so many opportunities, so many things you can execute on at a time. At any given time there's usually one thing you can be doing that will double revenue or double user growth. There's a lot of things that won't. Anything that doesn't make a large impact isn't much worth doing, so you focus on the big ticket items. 

Now, in the process of constantly focusing on what doubles you next, you'll find some blind spots, sometimes publicly.

Yeah, turns out, you actually do need to thoroughly test releases before pushing them out to hundreds of thousands of people. Yup, you should approve in-app purchases before the app goes live. No, you probably shouldn't have an 'Unlock for $4.99.' button that reads 'Unlock...', because you went a couple characters over at the last minute (...my bad.).

Those are all easy fixes, though. A better pre-release checklist, a more thorough testing before releases.

The bigger thing is strategic- what's the way you double in the next six months? For us, it's never been executing on the plan that took us though the last six months. It's coming up with something that goes in a slightly different direction, with a slightly different product focus. It also has to be a sustainable focus- if you're a private company, if you aren't taking VC, if you're in it to build a lasting business--- well, Red Bull just isn't going to cut it. You need to be able to kick ass on a regular basis.

A plan isn't a plan unless it works in the worst case scenario- I take my most conservative estimate and cut it in half. If we can double with that, we'll be in damned good shape in six months. This means a lot of excel geekery and it means a lot of quick tests to see if the underlying numbers are feasible. But, if those early signs are good, if those small-scale allocations work out, then it's time to go full-throttle. That's when it's time to set the overarching goal and execute.

That's prioritization.

Not a list. Not a set of 'strategic possibilities'. No, it's a a vision, a runthrough in excel, some quick tests, and a full-throttle blast to increasing revenue. Sexy? No. Profitable? Hell yeah.

For some reason people don't call insurance companies to insure their expensive electronic stuff. As it happens, insurance companies are good at this stuff!

It costs me $42/year to insure a 13" Macbook Pro, an iPhone 3GS, and a travel scanner. That includes if I drop my laptop, if a guitar head falls directly on the harddrive (...), or if it's stolen on the subte. Anything- it's real honest to god insurance, not insurance, as long as nothing actually goes wrong'. 

The best part is how easy it is- just call the local branch to get a contact, at which point you'll be able to email back and forth for everything, with the annual payment being withdrawn directly out of your checking account.

Q: What else have you learned from Soros?

A: I've learned many things from him, but perhaps most significant is that it's not whether you're right or wrong that's important, but how much money you make when you're right and how much you lose when you're wrong. The few times that Soros has ever criticized me was when I was really right on the market and didn't maximize the opportunity. 

As an example, shortly after I had started working for Soros, I was bearish on the dollar and put on a large short position against the Deutsche mark. The position had started going in my favor and I felt rather proud of myself. Soros came into my office, and we talked about the trade.

'How big a position do you have?' he asked.

'One billion dollars,' I answered.

'You call that a position?' he said dismissingly. He encouraged me to double my position. I did, and the trade went dramatically further in our favor.

Soros has taught me that when you have tremendous conviction on a trade, you have to go for the jugular. It takes courage to be a pig. It takes courage to ride a profit with huge leverage. As far as Soros is concerned, when you're right on something, you can't own enough.

Although I was not at Soros Management at the time, I've heard that prior to the Plaza Accord meeting in the fall of 1985, other traders in the office had been piggybacking George and hence were long the yen going into the meeting. When the yen opened 800 points higher on Monday morning, these traders couldn't believe the size of their gains and anxiously started taking profits. Supposedly, George came bolting out of the door, directing the other traders to stop selling the yen, telling them that he would assume their position. While these other traders were congratulating themselves for having taken the biggest profit in their lives, Soros was looking at the big picture: The government has just told him that the dollar was going to go down the next year, so why shouldn't he be a pig and buy more?

Soros is also the best loss taker I've ever seen. He doesn't care whether he wins or loses on a trade. If a trade doesn't work he's confident enough about his ability to win on other trades that he can easily walk away from the position. There are a lot of shoes on the shelf; wear only the ones that fit. If you're extremely confident, taking a loss doesn't bother you."